In a large bowl, beat cream cheese until fluffy. Add condensed milk, pudding mix, cold milk and vanilla until smooth. Fold in 1/2 of the whipped topping. Let sit for 5 minutes until in thickens.

In a microwave safe bowl, add the peanut butter and chocolate chips. Microwave on high in 30 seconds increments (stiring in between each time) until melted.

Line the bottom of a 13×9 inch dish with cookies. Pour 1/3rd of the chocolate mixture over the cookies. Top with 1/3rd of the pudding mix. Add as little or as much peanut butter cups over the pudding. Repeat layers. Top with remaining whipped topping, peanut butter cups, and drizzle of the chocolate sauce. Chill overnight. *Note- the longer this sits the better it tastes. The cookies really soften up nicely with it sits for 48 hours!